Carbone Derivatives of Group 14: A Class of Important Reactive Intermediates

doi:10.6023/A21120592

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (3): 373-385.DOI: 10.6023/A21120592 Previous Articles Next Articles

Review

十四族卡本衍生物: 一类重要的活性中间体

刘康^a, 李斌^a^,^b, 于吉攀^a^,^*(), 石伟群^a^,^*()

a 中国科学院高能物理研究所北京 100049
b 哈尔滨工程大学材料科学与化学工程学院哈尔滨 150001

投稿日期:2022-01-06 发布日期:2022-02-23
通讯作者: 于吉攀, 石伟群

作者简介:

刘康, 2016年6月毕业于湖北大学化学化工学院, 获理学学士学位; 2016.09~2021.12就读于中国科学院高能物理研究所无机化学专业并获博士学位, 导师为柴之芳院士和石伟群研究员. 2021.12~至今, 中国科学院高能物理研究所核能放射化学实验室博士后, 合作导师为石伟群研究员. 现主要从事低价态锕系元素与主族元素配合物的合成及成键性质的研究工作.

李斌, 2019年6月毕业于郑州大学化学学院, 获理学学士学位; 2019年9月至今为哈尔滨工程大学和中国科学院高能物理研究所联合培养研究生.

于吉攀, 博士, 副研究员. 2008年获江苏师范大学学士学位; 2011年获南开大学硕士学位; 2014年获清华大学博士学位; 2014.07~2016.07清华大学化学系博士后; 2016年7月加入中国科学院高能物理研究所核能放射化学实验室. 目前主要研究方向: 锕系元素化学.

石伟群, 研究员, 国家杰出青年科学基金获得者, 长期致力于核燃料循环化学与锕系元素化学相关基础研究, 在JACS、Angew. Chem、Chem、CCS Chem.、Nat. Commun、Adv. Mater.、Environ. Sci. Technol. 等国际知名期刊发表SCI 论文200余篇, 成果被国内外同行广泛关注和引用, 文章总引7400余次, H因子44 (Google Scholar). 分别担任英文期刊《Journal of Nuclear Fuel Cycle and Waste Technology》和《Journal of Nuclear Science and Technology》的编委与国际顾问编委, 中文期刊《核化学与放射化学》编委. 现为中国化学会核化学与放射化学专业委员会委员、中国核学会锕系物理与化学分会常务理事、中国有色金属学会熔盐化学与技术专业委员会副主任委员、中国核学会核化工分会理事兼副秘书长.

^† 共同第一作者

基金资助:
国家自然科学基金项目(21925603); 国家自然科学基金项目(21806167); 国家自然科学基金项目(22176191)

Carbone Derivatives of Group 14: A Class of Important Reactive Intermediates

Kang Liu^a, Bin Li^a^,^b, Jipan Yu^a(), Weiqun Shi^a()

a Laboratory of Nuclear Energy Chemistry, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100049, China
b College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China

Received:2022-01-06 Published:2022-02-23
Contact: Jipan Yu, Weiqun Shi
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(21925603); National Natural Science Foundation of China(21806167); National Natural Science Foundation of China(22176191)

The pursuit of unusual bonding environments of carbon species with non-octet electronic configurations has been quite active in fundamental organic and theoretical chemistry for many decades. In this respect, a distinct carbone species has been successfully isolated recently and defined as “carbodicarbene” or “bent allene.” Carbone is an important active intermediate since the synthesis of radical, carbene and carbyne. This neutral two-coordinated central carbon atom possesses two sets of lone pair electrons, possessing strong coordination ability. The present review introduces the discovery, fundamental properties and coordination chemistry of carbone. Meanwhile, the application of its relevant complexes in catalysis is introduced.

Key words: carbone, zero valence state of group 14 element, electronic structure, coordination chemistry, catalysis

Cite this article

Kang Liu, Bin Li, Jipan Yu, Weiqun Shi. Carbone Derivatives of Group 14: A Class of Important Reactive Intermediates[J]. Acta Chimica Sinica, 2022, 80(3): 373-385.

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Fig. & Tab. 29

Figure 1. Conceivable resonance structures of CDP

Figure 2. The bonding mode of carbone compound

Figure 3. Reactivity of carbodiphosphorane

Figure 4. Synthesis of CDP-UCl4, (CDP)2-UCl22+ and CDP-CeBr3(THF) adduct

Figure 5. Synthesis of CDP 14a and 14b

Figure 6. Synthesis of transition metal complexes 15~17 by CDP

Figure 7. Synthesis of cabone based on phenoxy

Figure 8. Synthesis of carbone 21 and the corresponding transition metal complexes 22

Figure 9. Hydrogenation of alkene catalyzed by Ru complexes

Figure 10. Synthesis of carbone 25 and corresponding [RhCl(CO)2(L)] complexes 27

Figure 11. Synthesis of carbone 28 and its reactivity

Figure 12. Synthetic routes toward carbone 35 and its palladium complex 36

Figure 13. Mizoroki-Heck reaction, Suzuki Coupling and C—N bond formation catalyzed by complex 36

Figure 14. Synthesis of phosphorus-based CDC and CDC-Rh complexes 39-41

Figure 15. Hydroamination, hydroheterarylation and hydroalkylation of dienes catalyzed by CDC-Rh complexes

Figure 16. Synthesis of chiral CDC-Rh complex and its application on hydroarylation

Figure 17. Synthesis of CDC based solely on carbon and the corresponding main group and transition-metal complexes

Figure 18. CDP catalyzed hydroboration of ketones and imines

Figure 19. Diffrent kinds of unsymmetric CDC ligand

Figure 20. Synthesis procedure for unsymmetric CDC ligand

Figure 21. Methylation of amine using CO2 based on carbone

Figure 22. Schematic representation of carbone, silyone and germylone

Figure 23. Synthesis of trisilaallene

Figure 24. Synthesis of CAAC-coordinated silyone complex 72

Figure 25. Synthesis of cyclic bis-NHC stabilized silyone and germylone

Figure 26. Reactivity of silyone complex 75

Figure 27. Synthesis of [SiNSi]GeGeFe

Figure 28. Synthesis of silyone complex 93

Figure 29. Synthesis of silyone and germylone derivatives and insight into the reactivity of silyone complex

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十四族卡本衍生物: 一类重要的活性中间体

Carbone Derivatives of Group 14: A Class of Important Reactive Intermediates

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